US4215213A - Process for producing a glycolipid ester - Google Patents

Process for producing a glycolipid ester Download PDF

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US4215213A
US4215213A US05/962,693 US96269378A US4215213A US 4215213 A US4215213 A US 4215213A US 96269378 A US96269378 A US 96269378A US 4215213 A US4215213 A US 4215213A
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ester
methyl
carbon atoms
group
reaction
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Shigeo Inoue
Yoshiharu Kimura
Manzo Kinta
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Kao Corp
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Kao Soap Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/226—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • This invention relates to glycolipid esters and in particular to a process for producing a glycolipid ester having surface activity and wax-like properties and represented by formula (I), ##STR2## wherein R 3 represents a hydrogen atom or a methyl group, R 4 represents a saturated or unsaturated hydrocarbon group having 12 to 16 carbon atoms when R 3 is hydrogen, R 4 represents a saturated or unsaturated hydrocarbon group having 11 to 15 carbon atoms when R 3 is methyl, and R represents a saturated or unsaturated alkyl group having 2 to 20 carbon atoms.
  • esters of sucrose (sugar esters) and higher fatty acid esters of anhydrosorbitol (Span) have been widely used as surface active agents, particularly in the field of emulsifying agents.
  • Such known esters are formed via the ester bonding between the hydroxy group of the sugar moiety and the higher fatty acid, and the surface activities of these esters are regulated according to their ester values.
  • Selective esterification of sugar at its desired position or positions is nearly impossible because many hydroxy groups exist in the sugar structure. In this situation, only mixtures of various ester isomers are utilized on an industrial basis.
  • the hydrophilic properties of these esters are significantly decreased as the ester values increase because the esters are formed by esterification of the hydroxy groups in the sugar.
  • esters are chemically unstable by reason of the fact that the ester bonds of the hydroxy groups in the sugar and higher fatty acid are more easily hydrolyzed than those of the common fatty alcohol esters.
  • R 3 and R 4 in formulas (IIa) and (IIb) are the same as defined above.
  • Sophoropilid is a mixture of many glycolipids, and its basic structure is of a [(2'-O- ⁇ -D-glycopyranosyl- ⁇ -D-glycopyranosyl)-oxy]-alkane acid or alkene acid which is obtained via the glycoside bonding between Sophorose and a long-chain fatty acid having a hydroxy group at the ⁇ or ⁇ -1 position.
  • the compound of the present invention possesses structural features which cannot be found in the conventional glycolipidtype surface active agents and which are characterized by the fact that a stable glycoside bond is formed by the hydroxyfatty acid and sugar and that the end group of the alkyl or alkenyl group is a reactive carboxyl group.
  • the compound has a greater chemical stability than those containing the conventional ester bonds because the hydrophobic alkyl or alkenyl group is linked to the hydrophilic group or sugar via glycoside bonding.
  • the alkyl or alkenyl group which has hydrophobic properties is occupied at its end by the reactive carboxyl group, and it is possible to produce glycolipids possessing surface activities and wax-like properties which have wide application by modification of the carboxyl groups only while leaving unmodified the hydroxy groups of the sugar moiety.
  • the production of the compound of formula (I) from Sophorolipid by fermentation involves some problems. Namely, Sophorolipid cannot be used as a starting material because it is a mixture of many homologs having a lactone ring, a free carboxyl group, acetyl groups and the like as shown in formulas (IIa) and (IIb). Accordingly, compound of formula (IIb-4) should be first produced by eliminating the acetyl groups and releasing the carboxyl group without destruction of the carbon framework.
  • the compound of formula (IIb-4) is a highly viscous substance peculiar to a sugar compound and is very difficult to obtain by means of conventional methods.
  • part of the deacetylated or deacylated compound acts as an emulsifying agent by incorporating the unreacted substances into micelles against continued attack by the remaining acid or alkali, thereby resulting in incomplete hydrolytic action.
  • the reaction proceeds to an extent of only about 50%, even if a given amount of potassium hydroxide (0.25 part per one part of Sophorolipid) is added to an aqueous solution containing 20% of Sophorolipid, and the resulting solution is hydrolyzed with heating for 6 hours.
  • hydrolysis is as incomplete as in the case where the alkali catalyst is employed, and partial cleavage of the glycosyl ether bond is caused as well as damage to the basic structure.
  • potassium hydroxide should be used in an amount of 0.25 part per one part of Sophorolipid, which is an extremely great amount of base which is uneconomical, and it is nearly impossible to separate the compound of the formula (IIb-4) which forms from the reaction solution by any industrially acceptable process.
  • the compound of formula (IIb-4) is readily soluble in water, and can be only dissolved in lower alcohols such as methanol and ethanol or special expensive organic solvents such as pyridine, dimethylsulfoxide or dimethylformamide which would otherwise create a serious obstacle to safety.
  • such compounds have a viscosity of more than 100,000 cps at room temperature.
  • an hydrous Sophorolipid of a low viscosity can be obtained by adding a small amount of at least one polyhydric alcohol represented by formulas (III) or (IV), ##STR4## wherein R 5 represents a hydrogen atom or a methyl group, R 6 and R 7 represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and m and n represent integers from 1 to 6, to hydrated Sophorolipid which is a fermentation product of Torulopsis bombicola, and distilling off water under reduced pressure by application of heat.
  • formulas (III) or (IV) ##STR4## wherein R 5 represents a hydrogen atom or a methyl group, R 6 and R 7 represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and m and n represent integers from 1 to 6, to hydrated Sophorolipid which is a fermentation product of Torulopsis bombicola, and distilling off water under reduced pressure by application of heat.
  • the present inventors have made an attempt to subject the above noted Sophorolipid of a lower viscosity to alcoholysis to deacetylate and cleave its lactone ring, and at the same time, esterify the free carboxyl group.
  • the reaction is very slow with the use of an alcohol having 2 or more carbon atoms and, that, for instance, ethanol requires an extended period of reaction time by a factor of approximately 110 times that of methanol, although methanolysis and methylation proceed rather rapidly to yield a compound wherein R in the formula (I) is a methyl group.
  • the compound of formula (I) can be obtained in a high purity and in high yield by producing, from Sophorolipid, methyl-[(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkanoate and -alkenoate of the formula (I) wherein R is a methyl group, and subjecting the resulting compound to an ester interchange reaction with an alcohol having 2 to 20 carbon atoms.
  • the invention provides a process for producing a glycolipid ester of the formula (I), which comprises subjecting Sophorolipid represented by formulas (IIa) and (IIb) to methanolysis and methylation reactions by reaction with methanol in the presence of a strong acid to produce methyl-[(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkanoate and -alkenoate represented by the formula (I), wherein R is a methyl group (hereinafter referred to as a glycolipid methyl ester) and an acetic acid methyl ester, distilling off the acetic acid methyl ester together with methanol as an azeotropic mixture, and subjecting the resulting mixture to ester interchange by reaction with an alcohol represented by the formula, ROH, wherein R is the same as defined above.
  • the glycolipid methyl ester is produced from Sophorolipid by adding at least one polyhydric alcohol represented by formulas (III) or (IV) to hydrated Sophorolipid, distilling off water under reduced pressure to produce the Sophorolipid-polyhydric alcohol system having a lower viscosity, and reacting the system with methanol in the presence of a strong acid.
  • Suitable polyhydric alcohols which are useful in the invention include, for example, ethyleneglycol, ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, ethyleneglycol monopropyl ether, diethyleneglycol, diethyleneglycol monomethyl ether, diethyleneglycol monoethyl ether, diethyleneglycol monobutyl ether, polyethyleneglycol having an average molecular weight of 150 to 280, propyleneglycol, dipropyleneglycol, tripropyleneglycol, tetrapropyleneglycol, pentapropyleneglycol, hexapropyleneglycol, propyleneglycol monomethyl ether, propyleneglycol monoethyl ether, propyleneglycol monopropyl ether, propyleneglycol monobutyl ether, dipropyleneglycol monomethyl ether, dipropyleneglycol monoethyl ether, tripropy
  • Methanolysis hardly proceeds with the use of a weak acid such as phosphoric acid.
  • a strong acid such as hydrochloric acid, sulfuric acid or nitric acid allows for rapid deacetylation and cleavage of the lactone ring, but the glycosyl ether bond is attacked under normal conditions of methylation whereby the basic structure is damaged. Because of these disadvantages, an attempt has been made to find the optimal reaction conditions under which alcoholysis and methylation are perfectly completed without the glycosyl ether bond being damaged.
  • the reaction proceeds advantageously with a strong acid such as hydrochloric acid, sulfuric acid or nitric acid in a concentration of from 0.05 to 0.50 N at a temperature of less than 45° C., and produces a single glycolipid methyl ester of the formula (I) wherein R is a methyl group.
  • a strong acid such as hydrochloric acid, sulfuric acid or nitric acid in a concentration of from 0.05 to 0.50 N at a temperature of less than 45° C.
  • the reaction is carried out with stirring for about 90 minutes, and the resulting mixture is subjected to thin layer chromatography.
  • the reaction is regarded as having become complete when only one Sophorolipid spot is observed on the thin layer.
  • reaction solution After being allowed to cool to room temperature, the reaction solution is neutralized with sodium hydroxide, potassium hydroxide or an alkali metal methylate.
  • the neutral salt which forms is filtered off, and the methyl acetate produced from the mother liquor and excess methanol are distilled off as an azeotropic mixture under normal pressure to such an extent that methanol remains in the residue in an amount of about 10% by weight of the reaction product.
  • the thus obtained reaction mixture is preferably used for subsequent reactions without any further treatment.
  • Ester interchange is carried out by reacting the glycolipid methyl ester with a desired alcohol in the presence of an alkaline agent.
  • alkali agents sodium hydroxide, potassium hydroxide and or alkali metal methylate are preferably used in an amount of 0.2 to 1.0% by weight of the reaction product containing about 10% of methanol.
  • the alcohol is preferably used in a molar ratio ranging from 1.1 to 1.2 relative to the glycolipid methyl ester.
  • the reaction is conducted with stirring at 70° to 80° C. under a reduced pressure of 100 to 200 mmHg while distilling off methanol as a solvent and the methanol produced by ester interchange.
  • the reaction is usually completed within from 30 minutes to 2 hours to afford the compound of formula (I) in a high yield.
  • the thus obtained compound according to this invention has both surface activity and wax-like properties, and exhibits the following superior characteristics in comparison to sugar esters of the conventional typical glycolipidtype surface active agents.
  • the monoester is about 18 to 14, the diester about 7, and the triester about 3 to 4 in their HLB values.
  • the HLB value variations are relatively small in the sugar esters.
  • the glycolipid ester has an HLB value of more than 20, and the compound of the formula (I) wherein R is C 2 H 5 or C 18 H 35 has an HLB of 6.
  • various glycolipid esters having a wide range of HLB values can be obtained by changing the number of carbon atoms of the alcohols.
  • glycolipid ethyl ester is about twice as high in forming power as the sugar ester (monooleate) and is also superior in detergency to the sugar ester.
  • glycolipid methyl ester forms a homogeneous emulsion containing extremely fine particles and possesses the same emulsifying ability as the sugar ester in less than half the amount of the sugar ester.
  • glycolipid methyl ester has good miscibility with various fats and oils, and hydrocarbon-type substances. This ester acts as an improving agent for fats and oils and the like, and is useful as a wax-like material.
  • the glycolipid methyl ester possesses excellent hydroscopic properties and water-keeping abilities comparable to that of lanolin as well as good wet-permeability because of its Sophorose residue.
  • the ester also has wax-like is because of the presence of the long-chain hydrophobic group. Therefore, when applied as an emulsifying agent, a wet-keeping agent or a moisturizer for cosmetics, the ester exerts a skin-protecting and feeling-improving effect which cannot be found in the conventional esters.
  • glycolipid methyl ester can be easily treated because of good solubility in water and many organic solvents and is chemically stable. Consequently, the ester finds wide application.
  • glycolipid methyl ester according to the invention possesses the above-mentioned superior properties; therefore, it may be utilized as a base or improvement additive for various cleansers, and fat and oil products for use with painting, printing, fiber processing, metal processing, stationery, cosmetics, drugs, agricultural chemicals, luster preservation, synthetic resins, paper manufacturing, machinery, leather and the like.
  • This product was degraded in a 5 N hydrochloric acidmethanol solution to give 2 moles of the methyl glycoside and 1 mole of the hydroxyfatty acid methyl ester, which were quantitatively analyzed by gas chromatography.
  • Example 2 To the mixture of methyl ester-polypropyleneglycol obtained in Example 1 were added 1.1 moles of an aliphatic alcohol relative to one mole of the methyl ester, and the resulting mixture was subjected to ester interchange by adding 0.5% by weight of sodium methylate. The methanol formed during the reaction was distilled off under normal or reduced pressure to obtain various desired aliphatic alcohol esters. The following are the preparation methods for some typical derivatives.
  • Example 2 To 20 g of the methyl ester-polypropyleneglycol obtained in Example 1 was added 20 g of ethanol to obtain a homogeneous solution to which was added 0.1 g of sodium methylate.
  • the ester interchange reaction was conducted at 70° C. while distilling off ethanol and methanol which gradually formed during the course of reaction. The mixture was neutralized with a sulfuric acidethanol solution and filtered. The filtrate was evaporated to eliminate ethanol to give 19 g of an ethyl ester.
  • the reaction progress was observed by measuring the area ratio of the gas chromatographic peaks of the methyl and ethyl esters obtained on a 3% silicon JXR-chromosolve W column having a particle size of 60-80 mesh and a helium gas stream of 0.6 kg/cm 2 at a column oven temperature of 310° C. with a hydrogen flame detector using a trimethylsililated product obtained with a trimethylsililating agent.
  • the reaction was terminated when the methyl ester peak disappeared.
  • Example 2 To 20 g of the methyl ester-polypropyleneglycol obtained in Example 1 was added 4.2 g of octyl alcohol, and to the mixture was added 5 g of methanol to obtain the homogeneous solution to which was then added 0.1 g of sodium methylate. The greater part of the methanol was distilled off at 70° C., and the ester interchange reaction was conducted while distilling off the formed methanol with stirring under a reduced pressure of 250 mmHg. The reaction progress was observed by gas chromatography as described above, and the reaction was terminated when the peak of the methyl ester disappeared. The mixture was neutralized with a fixed amount of citric acid to obtain 24 g of an octyl ester.
  • Example 2 To 20 g of the methyl ester-polypropyleneglycol obtained in Example 1 were added 6.1 g of lauryl alcohol, 5 g of methanol and then 0.1 g of sodium methylate. Thereafter, the same procedure as in the above process (2) was repeated to yield 26 g of a lauryl ester.
  • octyl ester, lauryl ester and oleyl ester were purified by column chromatography on silica gel, and the resulting pure products were all white paste substances.
  • the IR absorption spectra and NMR spectra of these products were the same with the exception of the differences of the methyl ester spectra and of the absorption strength of the methylene groups.
  • the octyl ester was decomposed in a 5 N hydrochloric acidmethanol solution to obtain 2 moles of the methyl glycoside, 1 mole of the hydroxyfatty acid methyl ester and 1 mole of the octyl alcohol.
  • the lauryl ester yielded 2 moles of the methyl glycoside, 1 mole of the hydroxy fatty acid methyl ester and 1 mole of the lauryl alcohol
  • the oleyl ester gave 2 moles of the methyl glycoside, 1 mole of the hydroxy fatty acid methyl ester and 1 mole of the oleyl alcohol.

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US05/962,693 1978-02-17 1978-11-21 Process for producing a glycolipid ester Expired - Lifetime US4215213A (en)

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675392A (en) * 1982-06-23 1987-06-23 Svenska Sockerfabriks Ab Glycosides
US4797481A (en) * 1986-08-28 1989-01-10 Raffineria Olii Lubrificanti "R.O.L." S.P.A. Surfactants derived from di- or tri-carboxylic hydroxy-acids
US4870010A (en) * 1984-10-16 1989-09-26 Petroleum Fermentations N.V. Bioemulsified-containing personal core products for topical application to dermopathologic conditions of the skin and scalp
US4999195A (en) * 1984-10-16 1991-03-12 Emulsan Biotechnologies Inc. Personal care products containing bioemulsifiers
US5654192A (en) * 1992-12-30 1997-08-05 Institut Francais Du Petrole Composition containing a surface active compound and glycolipids and decontamination process for a porous medium polluted by hydrocarbons
EP0745608A3 (de) * 1995-05-29 1997-12-17 Hoechst Aktiengesellschaft Neuartige Glukose- und Sophoroselipide, ein Verfahren zu deren Herstellung un deren Verwendung
WO1999024448A3 (de) * 1997-11-07 1999-08-19 Aventis Res & Tech Gmbh & Co Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung
US20060199244A1 (en) * 2005-03-01 2006-09-07 Ashby Richard D Production of open-chained sophorolipids
US20070249542A1 (en) * 2003-03-24 2007-10-25 Gross Richard A Treatment and prophylaxis of sepsis and septic shock
WO2011154523A1 (en) 2010-06-11 2011-12-15 Universiteit Gent Yeast strains modified in their sophorolipid production and uses thereof
US9351485B2 (en) 2009-09-29 2016-05-31 Evonik Degussa Gmbh Use of sophorolipids and derivatives thereof in combination with pesticides as adjuvant/additive for plant protection and the industrial non-crop field
US10196663B2 (en) 2014-03-31 2019-02-05 The Regents Of The University Of California Methods of producing glycolipids
CN109876731A (zh) * 2018-12-25 2019-06-14 泰伦特生物工程股份有限公司 一种胞外多糖发酵废液和槐糖脂复配生物乳化剂及制备方法和应用
CN114106807A (zh) * 2020-08-27 2022-03-01 中国石油化工股份有限公司 一种改性槐糖脂组合物、其制备方法及应用
CN114479866A (zh) * 2020-10-23 2022-05-13 中国石油化工股份有限公司 一种生物型淋洗剂、其制备方法及应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE77048T1 (de) * 1984-10-16 1992-06-15 Emulsan Biotechnologies Inc Bioemulgatoren enthaltende kosmetische und pharmazeutische zusammensetzungen.
JP6611221B2 (ja) * 2014-06-12 2019-11-27 花王株式会社 ソフォロリピッドの製造方法
WO2018179026A1 (ja) 2017-03-27 2018-10-04 ユニサンティス エレクトロニクス シンガポール プライベート リミテッド 柱状半導体装置と、その製造方法

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US2931797A (en) * 1957-07-02 1960-04-05 Corn Products Co Mixed methyl glucoside-glycerol fatty acid ester emulsifiers
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils
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US3634397A (en) * 1969-05-16 1972-01-11 Procter & Gamble Complete short-chain esters of polyol mono-(acidic lipid) esters
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Patent Citations (7)

* Cited by examiner, † Cited by third party
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US2602789A (en) * 1949-08-23 1952-07-08 Joseph H Schwartz Ether-esters of polyhydroxy compounds
US2931797A (en) * 1957-07-02 1960-04-05 Corn Products Co Mixed methyl glucoside-glycerol fatty acid ester emulsifiers
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils
US3585185A (en) * 1968-05-13 1971-06-15 Wyandotte Chemicals Corp Ester-containing polyols
US3631025A (en) * 1969-05-16 1971-12-28 Procter & Gamble Polyol mono-(acidic lipid) esters
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675392A (en) * 1982-06-23 1987-06-23 Svenska Sockerfabriks Ab Glycosides
US4870010A (en) * 1984-10-16 1989-09-26 Petroleum Fermentations N.V. Bioemulsified-containing personal core products for topical application to dermopathologic conditions of the skin and scalp
US4999195A (en) * 1984-10-16 1991-03-12 Emulsan Biotechnologies Inc. Personal care products containing bioemulsifiers
US4797481A (en) * 1986-08-28 1989-01-10 Raffineria Olii Lubrificanti "R.O.L." S.P.A. Surfactants derived from di- or tri-carboxylic hydroxy-acids
US5654192A (en) * 1992-12-30 1997-08-05 Institut Francais Du Petrole Composition containing a surface active compound and glycolipids and decontamination process for a porous medium polluted by hydrocarbons
EP0745608A3 (de) * 1995-05-29 1997-12-17 Hoechst Aktiengesellschaft Neuartige Glukose- und Sophoroselipide, ein Verfahren zu deren Herstellung un deren Verwendung
US5767255A (en) * 1995-05-29 1998-06-16 Hoechst Aktiengesellschaft Glucose- and sophorose-lipids, a process for their preparation and their use
WO1999024448A3 (de) * 1997-11-07 1999-08-19 Aventis Res & Tech Gmbh & Co Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung
US6433152B1 (en) 1997-11-07 2002-08-13 Aventis Research & Technologies Gmbh & Co Kg Sophoroselipids, method for their production and use
US20070249542A1 (en) * 2003-03-24 2007-10-25 Gross Richard A Treatment and prophylaxis of sepsis and septic shock
US7772193B2 (en) * 2003-03-24 2010-08-10 Polytechnic University of NYU Treatment and prophylaxis of sepsis and septic shock
US20060199244A1 (en) * 2005-03-01 2006-09-07 Ashby Richard D Production of open-chained sophorolipids
US9351485B2 (en) 2009-09-29 2016-05-31 Evonik Degussa Gmbh Use of sophorolipids and derivatives thereof in combination with pesticides as adjuvant/additive for plant protection and the industrial non-crop field
WO2011154523A1 (en) 2010-06-11 2011-12-15 Universiteit Gent Yeast strains modified in their sophorolipid production and uses thereof
US10196663B2 (en) 2014-03-31 2019-02-05 The Regents Of The University Of California Methods of producing glycolipids
CN109876731A (zh) * 2018-12-25 2019-06-14 泰伦特生物工程股份有限公司 一种胞外多糖发酵废液和槐糖脂复配生物乳化剂及制备方法和应用
CN109876731B (zh) * 2018-12-25 2021-06-01 泰伦特生物工程股份有限公司 一种胞外多糖发酵废液和槐糖脂复配生物乳化剂及制备方法和应用
CN114106807A (zh) * 2020-08-27 2022-03-01 中国石油化工股份有限公司 一种改性槐糖脂组合物、其制备方法及应用
CN114106807B (zh) * 2020-08-27 2023-05-05 中国石油化工股份有限公司 一种改性槐糖脂组合物、其制备方法及应用
CN114479866A (zh) * 2020-10-23 2022-05-13 中国石油化工股份有限公司 一种生物型淋洗剂、其制备方法及应用
CN114479866B (zh) * 2020-10-23 2024-02-09 中国石油化工股份有限公司 一种生物型淋洗剂、其制备方法及应用

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JPS54109913A (en) 1979-08-29
DE2905295C2 (enrdf_load_stackoverflow) 1988-02-18
DE2905295A1 (de) 1979-08-30
JPS5639317B2 (enrdf_load_stackoverflow) 1981-09-11

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